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House vacation rentals in Southold

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Top-rated house rentals in Southold

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Home in North Fork

4.82 out of 5 average rating, 201 reviews

The Greenport Townhouse - Amazing Location & Large Backyard

The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer. Guests have access to the entire house and backyard area. We respect your privacy, but we are accessible if you have questions or need anything throughout your stay. Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby. We are just a few short blocks from the Hampton Jitney stop, the LIRR station, and the Shelter Island Ferry. No car necessary - you can walk wherever you need!

Home in Shelter Island

4.95 out of 5 average rating, 224 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.

Home in North Fork

4.98 out of 5 average rating, 131 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals available (inquire!)

Home in East Haven

4.96 out of 5 average rating, 132 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Home in East Hampton

4.95 out of 5 average rating, 409 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and check-out are NOT available in season

Home in Southampton

4.9 out of 5 average rating, 247 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

Home in North Fork

4.95 out of 5 average rating, 334 reviews

The Sandpiper

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Home in North Fork

4.93 out of 5 average rating, 103 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Home in North Fork

4.91 out of 5 average rating, 101 reviews

North Fork Escape - Walk To Village, Beach, Parks

Modern & cozy 3-bedroom, 2-bathroom farmhouse, dating back to 1905 and in walking distance of Greenport village and its many attractions. Large, landscaped & fully fenced private backyard for relaxed summer days and nights. Wood burning fireplace for the cooler months. Walk to the great bars & restaurants, beaches, train station/jitney & a short drive to the wineries & farm stands of the North Fork. Central heat & AC with new baths added in 2022.

Home in North Fork

4.93 out of 5 average rating, 117 reviews

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Home in North Fork

4.97 out of 5 average rating, 201 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Home in North Fork

4.98 out of 5 average rating, 243 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

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Popular amenities for Southold house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in East Hampton

4.93 out of 5 average rating, 107 reviews

Private & Pristine with Pool and Kid’s Playard

Home in Water Mill

4.92 out of 5 average rating, 120 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Home in Sag Harbor

4.81 out of 5 average rating, 133 reviews

Thanksgiving! Sag Harbor Gem!

Home in Manorville

4.98 out of 5 average rating, 243 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Home in Mastic Beach

4.93 out of 5 average rating, 118 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Home in Southampton

4.95 out of 5 average rating, 151 reviews

Waterview, DogsStayFree! Kayaks, Ping-Pong

Home in East Hampton

4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

Home in Water Mill

4.92 out of 5 average rating, 119 reviews

Astounding Watermill 5 Bedroom home with Pool

Weekly house rentals

Home in North Fork

5 out of 5 average rating, 10 reviews

Sunset Ranch

Home in North Fork

4.98 out of 5 average rating, 53 reviews

Victorian Pearl

Home in North Fork

4.93 out of 5 average rating, 15 reviews

Charming Home in Village Center!

Home in North Fork

5 out of 5 average rating, 11 reviews

Modern Farmhouse Oasis in GP Village

Home in North Fork

5 out of 5 average rating, 4 reviews

Peaceful in Peconic

Home in North Fork

4.92 out of 5 average rating, 24 reviews

North Fork Farmhouse with Saltwater Pool

Home in North Fork

5 out of 5 average rating, 6 reviews

North Fork Farm House

Home in North Fork

4.92 out of 5 average rating, 12 reviews

North Fork Sound Front Home with Pool

Private house rentals

Home in North Fork

5 out of 5 average rating, 23 reviews

Elegant Victorian in the Heart of Greenport

Home in North Fork

5 out of 5 average rating, 17 reviews

Newly renovated farmhouse - steps to Village

Home in North Fork

5 out of 5 average rating, 12 reviews

Peaceful Guesthouse

Home in North Fork

5 out of 5 average rating, 16 reviews

Waterfront with private dock & bocce court

Home in North Fork

5 out of 5 average rating, 3 reviews

Bahia Mar: Beach House, North Fork

Home in North Fork

4.94 out of 5 average rating, 70 reviews

Beach house @ NoFo

Home in North Fork

5 out of 5 average rating, 25 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

Home in North Fork

4.95 out of 5 average rating, 63 reviews

Nassau Point, North Fork Home w/ Pool

Quick stats about house rentals in Southold

Total rentals
170 properties
Nightly prices starting at
$130 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
50 properties have a pool

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